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Preparation method of 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone

A technology of dimethoxyl and androstenedione, which is applied in the fields of biomedicine and chemical synthesis, can solve the problems of high price, high synthesis cost, and unsuitability for industrial production, and achieve low production cost, stable and reliable quality, and high yield high effect

Pending Publication Date: 2022-03-29
湖南普尔生物医药有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

This method also uses expensive nandrolone as a starting material, and the synthesis cost is high, so it is not suitable for industrial production

Method used

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  • Preparation method of 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone
  • Preparation method of 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone
  • Preparation method of 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0084] Preparation of Compound A:

[0085] First, 20kg of 19-nor-4-androstenedione and 80L of acetic anhydride (86.4kg) were added into the reaction kettle and mixed evenly. Then 0.4kg of p-toluenesulfonic acid was added and the reaction was stirred at room temperature for 5h. After the reaction was complete as detected by TLC, the reaction solution was poured into ice water for crystallization, centrifugally filtered, the filter cake was washed 3 times with water, and dried to obtain 23kg of white crystalline compound A with a yield of 115%, Mp: 149-151°C.

Embodiment 2

[0087] Preparation of Compound A:

[0088] First, 20kg of 19-nor-4-androstenedione and 80L of acetic anhydride (86.4kg) were added into the reaction kettle and mixed evenly. Then add 0.5kg pyridine hydrochloride and stir the reaction at room temperature for 5h. After the reaction was complete as detected by TLC, the reaction solution was poured into ice water for crystallization, centrifugally filtered, the filter cake was washed 3 times with water, and dried to obtain 21kg of white crystalline compound A with a yield of 105%, Mp: 149-151°C.

Embodiment 3

[0090] Preparation of Compound B:

[0091] 10kg of compound A was dissolved in 40LN,N-dimethylformamide (37.92kg), cooled to 0°C, then 6kg of N-bromosuccinimide was added and the reaction was stirred at room temperature for 1h, and the reaction was detected by TCL until the end of the reaction. Then add 8 kg of calcium carbonate to continue the reaction at a temperature of 80° C., and TCL detects that the reaction ends. After filtration, the filtrate was poured into a sufficient amount of ice water for crystallization, and then filtered to obtain 6.7kg of light yellow crystalline compound B with a yield of 67%, mp: 178-180°C.

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Abstract

The invention discloses a novel method for synthesizing 7 [alpha]-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone, and relates to the technical field of chemical synthesis of 7 [alpha]-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone. According to the method, 19-nor-4-androstenedione which is easy to obtain in the market is used as a raw material, and an intermediate 7 alpha-methyl-19-nor-4-androstenedione is obtained after an acylation reaction, a bromination reaction, a debromination reaction and a methylation reaction are carried out in sequence; then, the 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone is sequentially subjected to a ketalation reaction, a hydrolysis reaction and an etherification reaction, and 7 alpha-methyl-3, 3-dimethoxy-5 (10)-androstene-17-ketone is obtained. The method has the advantages of easily available raw materials, short synthetic reaction steps and low production cost, and the crude product obtained by the method is simple in later purification treatment, high in yield and suitable for industrial production.

Description

technical field [0001] The invention relates to a method for synthesizing medicine, in particular to a method for preparing 7α-methyl-3,3-dimethoxy-5(10)-androsten-17-one, which belongs to biomedicine and chemical synthesis technology field. Background technique [0002] A 7α-methyl-3,3-dimethoxy-5(10)-androsten-17-one, CAS accession number: 88247-84-1. The compound is a key intermediate for preparing medicines such as tibolone and tritorone. Tibolone has androgenic activity and weak progestin activity, and has obvious anabolic effect, which can prevent postmenopausal menopausal syndrome such as women's osteoporosis, reduce facial flushing, sweating and other menopausal symptoms, and is used for the treatment of menopause and menopause. Drug of choice for post-syndrome. [0003] Prior Art 1: N.P.VAN VLIET, A.I.A.BROESS, J.A.M.PETERS, et al.AnAlternative synthesis of 17β-Hydroxy-7α-methyl-19-nor-17α-pregn-5(10)-en-20-yn-3- one(Org OD14).Recl.Trav. discloses a preparation ...

Claims

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Application Information

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IPC IPC(8): C07J1/00
CPCC07J1/0059Y02P20/55
Inventor 肖方青郑济华丁峰
Owner 湖南普尔生物医药有限公司
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